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Stages of Our Entrepreneurial Journey



Sometimes it’s difficult to know where to focus our time, resources, and energy as entrepreneurs. Our friends at Cultivate Advisors held an event recently at Haven to help us pinpoint the stage we are in so that we can best determine what we need to focus on in order to grow to the next stage in this journey.

The 5 stages of the entrepreneurial journey identified are:

  1. Hustler

  2. Experimenter

  3. Visionary

  4. Systemizer

  5. Influencer

In order to move forward, you have to know where you are, so take the quiz here to know which stage you’re in. Once you identify the stage, keep reading for tips and tricks to move up to the next stage.


Most Hustlers know it. They’re running the show solo, in the early days of their business, and wear ALL the hats. This is the stage where you’ll be grinding, focusing on revenue and sales with a huge sense of urgency. Spend frugally, leverage your vendors and connections, and use your small size to your advantage. Being small allows you to be nimble, pivoting when necessary. Daily activities typically drive you at this stage.


Still hustling, but with the flexibility to increase trial and error and test out some new ideas. Experimenters likely have hired an employee or two with the entrepreneurial spirit they’ll need to continue growing the business and sharing all those hats. You’re still involved in all of the decisions but you’re starting to measure data so you’re able to streamline a bit and feel more confident in those decisions, while still highly focused on sales. Weekly activities typically drive you at this stage.


Visionaries can be proud of the company they’ve built and grown. You likely have hired more than 5 people to work alongside you, and with them you are able to support the sales efforts in new ways, putting in place accountability measures, KPIs, and you should feel good about the pro forma’s you’re creating. Monthly activities typically drive you at this stage.


As a systemizer, your employees can begin to feel like leaders in their own right. You’ve chosen your team well and you’re scaling with systems, automating and hiring specialists. You are focusing on this team by creating robust on-boarding and training programs. You can start loosening your grip and share your vision. Your team will help you reach it. Quarterly activities typically drive you at this stage.


This stage of the journey feels pretty good, but you’ll have to put in the time to develop your leadership team for either the exit you’ve dreamed of or the handoff you’ve planned for. Making sure you’re company is recession-proof and has sustainability is a key driver by now. Annual activities typically drive you at this stage.

At each stage of this journey, entrepreneurs can expect to let go of more and rely on others. We will each also start taking longer and longer views, so that the teams we’ve built can handle the day-to-day activities that drove us in the beginning. If you’d like to know more, we highly recommend reaching out to Cultivate Advisors.

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